“Should I stay or should I go” is the wrong shape of question, and it is why people circle this decision for years. The real problem is that the two sides are measured in different units — and almost nobody converts one before comparing them.
A salary has already had payroll tax taken out of it, and it quietly includes a health premium and a retirement contribution somebody else pays. A self-employed figure includes none of that. It owes the whole 15.3% self-employment tax rather than an employee’s 7.65%. It buys its own insurance. And it is earned across whatever hours are left once you have finished selling, invoicing and chasing payment.
Put an untouched salary next to an untouched freelance rate and the comparison is not close to fair. The Career-Pivot Decision Helper does the conversion first — a weighted scorecard that ranks staying in your job against going self-employed across thirteen criteria — and only then asks you what else matters.
Three of the thirteen criteria refuse to be guessed
Ten of the criteria are judgments only you can make: how stable the income would be, how much autonomy you would have, whether the work is work you actually want to do, whether the household is genuinely behind it, how easily you could get back.
The other three are arithmetic — Total Compensation, Effective Hourly Rate and Runway & Downside Risk — and rating arithmetic by feel gets it wrong in a predictable direction. So the money tabs compute them from your own numbers, then stretch your paths between the best on your grid (5) and the worst (1). That is what lets a paycheck and a life be weighed on one scale without either winning simply by being measured in bigger-sounding numbers.
What each path really pays
The Income & Hours tab takes each path’s wages, self-employed revenue, business expenses and hours, and works out the employment tax properly for whatever mix you enter: employee FICA at 7.65% on wages, self-employment tax at 15.3% on 92.35% of net profit, or both at once for a hybrid. The two share one Social Security wage base, and wages consume it first — which is why a hybrid path’s tax is never simply the sum of a job’s and a side business’s.
It also computes the qualified business income deduction — up to 20% of qualified business income — and the self-employed health premium deduction, which is real money on a self-employed path and which the workbook switches off for any path that has an employer plan attached to it. (The rule also removes it for any month a spouse’s employer plan was open to you; that one you check yourself.)
Then Benefits & Total Comp adds the health premium and retirement contribution an employer makes on your behalf and subtracts the coverage you would have to buy for yourself. For private-industry workers in the United States, benefits made up 30.1% of total compensation in March 2026 (US Bureau of Labor Statistics, Employer Costs for Employee Compensation (opens in new tab), March 2026 release). So leaving a job means replacing roughly a third of your total compensation before you have earned a cent more. (That BLS page is the current release and is updated quarterly.)
Two numbers come out: total effective annual compensation and effective hourly rate. The second is the one most likely to change the answer, because it counts the selling, the invoicing, the bookkeeping, the unpaid weeks — and, on both sides, the commute.
Twelve working arrangements, already researched
Pick a path type from the dropdown and the structural facts fill in: who withholds your payroll tax, who funds your health insurance and retirement, whether time off is paid, how volatile the income is, who absorbs a bad quarter, and how hard the arrangement is to undo. Twelve types are covered — employee, agency contractor, 1099 freelancer, single-member LLC, an LLC with an S-corp election, a product business, a co-founder, a franchise, a hybrid, and more.
Alongside them sits the 2026 tax reference behind the engine:
- the 15.3% self-employment tax and the 92.35% net-earnings factor
- the $184,500 Social Security wage base, and employee FICA
- the additional Medicare tax (documented for reference — the workbook does not model it)
- the qualified business income deduction of up to 20%
- the estimated-tax due dates and the safe harbor
- COBRA at up to 102% of the full premium for up to 18 months
- what benefits are worth on average
Every figure is named, dated and sourced, on the tab and in a printable guide.
Can you actually get there from here?
A path that pays well in year three is not the safer choice if it runs out of road in month nine. The Runway & Risk tab takes your savings, what the household genuinely has to spend each month and any other income, and asks of each path: how long could you live on this while it gets going — and how long if it earns only 60% of what you are assuming?
That 40% haircut is deliberate, not pessimism. The answer becomes a cushion: months of worst-case runway beyond the ramp this kind of path starts with — a conservative planning default, stated as one on the tab, that you overwrite with what you know about your own trade. A negative cushion is not a verdict on the idea. It is a timing problem, and it is worth knowing which of the two you have.
The result, and the price of fit
Results & Ranking puts every path in order with its total compensation, its effective hourly rate and its worst-case runway beside it, names where each one is strongest and weakest, and reports the margin over the runner-up — telling you plainly whether this is a clear call or a coin toss.
It also names the price of fit: what choosing your best-fitting path over your best-paying one costs per year, and across your whole planning horizon. That is not an argument against it. It is a price, made visible, so you can decide on purpose whether what you are buying with it is worth having. Whether it is, is your call — but it is now a call you make with a figure in front of you.
Only need the runway math? That part is free
If your question is only when could I afford to leave, on cash alone, you do not need a workbook and you should not pay for one — we give that away as the free “Should I Quit My Day Job?” runway calculator, which runs on Ardent Seller, our software for makers, and answers in about a minute.
This workbook is for the harder question underneath it: which path is actually better, once the money, the hours, the benefits and everything you cannot put a number on are weighed together.
Staying is a choice, not the absence of one
The workbook puts your current job in the first column with a real salary, real benefits, a real ceiling and a real rating on every row — and it is a genuine contender that a half-decided grid never makes room for. When it loses, it now loses on rows you can name.
It also makes room for the two paths people forget to score: a different job, which can fix most of what is actually wrong for none of the risk, and a hybrid that keeps the paycheck while you find out whether anybody will pay. The worked example that ships in the file is honest about where those land.
Own it, don’t rent it
Between a blank spreadsheet — infinite work, and you still have to invent the tax arithmetic — and a career coach on a monthly retainer sits a file you own outright. No login, no subscription, no seat. Rerun it in eighteen months when the numbers have changed, or the day an offer arrives, or when somebody you love is facing the same question.
It opens in Excel, Google Sheets and LibreOffice Calc, and the Google Sheets version is a real one-click copy of a native Sheet, not an import you have to repair.
A decision aid, not advice: this is a decision-making and planning template, not tax, financial, legal, employment or career advice. The example paths and their numbers are illustrative. The tax figures are sourced and dated in the file, and three simplifications are stated plainly in it — income tax is a single blended rate you set yourself, an S-corp election is modeled as an ordinary sole proprietorship, and the additional Medicare tax is not modeled. A weighted score is a tool for thinking, never a verdict you have to obey.
